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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1638.
Published online 2010 November 24. doi:  10.1107/S160053681004715X
PMCID: PMC3011745

catena-Poly[[bis­(acetato-κ2 O,O′)cobalt(II)]-μ-4,4′-bis­(benzimidazol-1-yl)biphenyl-κ2 N 3:N 3′]

Abstract

In the title one-dimensional coordination polymer, [Co(C2H3O2)2(C26H18N4)]n, the CoII atom (site symmetry 2) is coordinated by two O,O′-bidentate acetate ions and two 4,4′-bis­(benzimidazol-1-yl)biphenyl ligands in a distorted cis-CoN2O4 octa­hedral geometry. The bridging ligand, which is completed by crystallographic twofold symmetry, links the CoII atoms into [10An external file that holds a picture, illustration, etc.
Object name is e-66-m1638-efi1.jpg] chains. Within the ligand, the dihedral angle between the benzene and benzimidazole rings is 48.31 (8)°.

Related literature

For background to benzimidazole-derived ligands in coordin­ation polymers, see: Jin et al. (2006 [triangle]); Li et al. (2010 [triangle]); Su et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1638-scheme1.jpg

Experimental

Crystal data

  • [Co(C2H3O2)2(C26H18N4)]
  • M r = 563.46
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1638-efi2.jpg
  • a = 13.078 (3) Å
  • b = 16.348 (3) Å
  • c = 11.354 (2) Å
  • V = 2427.5 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.75 mm−1
  • T = 293 K
  • 0.25 × 0.22 × 0.18 mm

Data collection

  • Rigaku CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.828, T max = 0.873
  • 21778 measured reflections
  • 2150 independent reflections
  • 2101 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.083
  • S = 1.10
  • 2150 reflections
  • 178 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004715X/hb5708sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004715X/hb5708Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Benzoimidazole has been well used in crystal engineering, and a large number of benzoimidazole-containing flexible ligands have been extensively studied (Su et al.,2003; Jin et al.,2006). However, to our knowledge, the research on benzoimidazole ligands bearing rigid spacers is still less developed (Li et al.,2010).

Single-crystal X-ray diffraction analysis reveals that the title compound (I) crystallizes in the orthorhombic space group Pbcn. The geometry of the CoII ion is surrounded by two benzoiimidazole rings of distinct L ligands and two chelated acetate anions, which illustrates a slightly distorted octahedral coordination environment (Fig. 1). Notably, as shown in Fig. 2, the six-coordinated CoII center is bridged by the linear ligand L to form an infinite one-dimensional architecture.

Experimental

A mixture of CH3OH and CHCl3 (1:1, 8 ml), as a buffer layer, was carefully layered over a solution of 4,4'-bis(benzoimidazol-1-yl)terphenyl (L, 0.06 mmol) in CHCl3 (6 ml). Then a solution of Co(CH3COO)2 (0.02 mmol) in CH3OH (6 ml) was layered over the buffer layer, and the resultant reaction was left to stand at room temperature. After ca three weeks, purple blocks of (I) appeared at the boundary. Yield: ~25% (based on L).

Refinement

C-bound H atoms were positioned geometrically and refined in the riding-model approximation, with C—H = 0.93Å and Uiso(H) = 1.2Ueq.

Figures

Fig. 1.
The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radius.
Fig. 2.
The crystal packing for (I).

Crystal data

[Co(C2H3O2)2(C26H18N4)]Dx = 1.542 Mg m3
Mr = 563.46Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcnCell parameters from 6002 reflections
a = 13.078 (3) Åθ = 2.0–27.9°
b = 16.348 (3) ŵ = 0.75 mm1
c = 11.354 (2) ÅT = 293 K
V = 2427.5 (8) Å3Block, purple
Z = 40.25 × 0.22 × 0.18 mm
F(000) = 1164

Data collection

Rigaku CCD area-detector diffractometer2150 independent reflections
Radiation source: fine-focus sealed tube2101 reflections with I > 2σ(I)
graphiteRint = 0.038
Detector resolution: 9 pixels mm-1θmax = 25.0°, θmin = 2.7°
ω scansh = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −19→19
Tmin = 0.828, Tmax = 0.873l = −13→13
21778 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0367P)2 + 2.7447P] where P = (Fo2 + 2Fc2)/3
2150 reflections(Δ/σ)max < 0.001
178 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.41 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Co10.00000.40968 (2)0.25000.01345 (14)
O10.08394 (11)0.37040 (10)0.39033 (14)0.0268 (4)
C110.45996 (14)0.51680 (12)−0.20359 (17)0.0138 (4)
C120.44299 (15)0.44856 (12)−0.13277 (18)0.0160 (4)
H120.48000.4009−0.14610.019*
C70.23045 (15)0.58691 (12)0.15147 (17)0.0134 (4)
C30.11760 (15)0.61095 (13)0.31741 (17)0.0163 (4)
H30.06330.59560.36550.020*
N20.24267 (12)0.52419 (10)0.06971 (14)0.0140 (4)
N10.11225 (12)0.48650 (10)0.18429 (14)0.0148 (4)
C100.40024 (15)0.58655 (13)−0.18495 (18)0.0171 (4)
H100.40960.6322−0.23270.021*
C130.37154 (15)0.45080 (12)−0.04256 (18)0.0162 (4)
H130.36180.40540.00550.019*
C80.31481 (14)0.52118 (12)−0.02460 (17)0.0144 (4)
C90.32729 (15)0.58878 (12)−0.09655 (18)0.0164 (4)
H90.28720.6351−0.08570.020*
C140.02557 (15)0.31459 (12)0.42490 (18)0.0163 (4)
O2−0.06065 (12)0.30382 (10)0.38106 (15)0.0292 (4)
C40.17056 (15)0.68295 (13)0.33635 (18)0.0184 (4)
H40.15170.71650.39890.022*
C10.17101 (15)0.46685 (12)0.09472 (17)0.0153 (4)
H10.16410.41840.05260.018*
C150.06315 (17)0.25921 (14)0.5229 (2)0.0249 (5)
H15A0.06360.28890.59580.037*
H15B0.13120.24080.50520.037*
H15C0.01850.21280.52970.037*
C20.14891 (15)0.56223 (12)0.22333 (17)0.0140 (4)
C60.28339 (15)0.65947 (12)0.16999 (17)0.0162 (4)
H60.33720.67530.12160.019*
C50.25205 (16)0.70673 (13)0.26368 (18)0.0176 (4)
H50.28580.75570.27920.021*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co10.0112 (2)0.0150 (2)0.0141 (2)0.0000.00353 (14)0.000
O10.0208 (8)0.0286 (9)0.0311 (9)−0.0010 (7)0.0001 (7)0.0116 (7)
C110.0112 (9)0.0182 (11)0.0121 (9)−0.0018 (8)0.0014 (8)−0.0006 (8)
C120.0148 (10)0.0151 (10)0.0182 (10)0.0020 (8)0.0026 (8)−0.0013 (8)
C70.0132 (10)0.0144 (10)0.0126 (9)0.0016 (7)0.0007 (8)0.0005 (8)
C30.0146 (10)0.0214 (11)0.0131 (10)0.0008 (8)0.0029 (8)0.0006 (8)
N20.0134 (8)0.0153 (8)0.0133 (8)−0.0009 (6)0.0049 (7)−0.0002 (7)
N10.0145 (8)0.0154 (9)0.0146 (8)−0.0018 (7)0.0037 (7)−0.0016 (7)
C100.0173 (10)0.0173 (11)0.0167 (10)0.0001 (8)0.0041 (8)0.0032 (8)
C130.0176 (10)0.0144 (10)0.0166 (10)−0.0023 (8)0.0035 (8)0.0012 (8)
C80.0109 (9)0.0189 (10)0.0135 (10)−0.0017 (8)0.0042 (8)−0.0012 (8)
C90.0141 (10)0.0166 (10)0.0184 (10)0.0031 (8)0.0036 (8)0.0001 (8)
C140.0138 (10)0.0187 (10)0.0165 (10)0.0023 (8)0.0040 (8)−0.0055 (8)
O20.0279 (9)0.0226 (8)0.0372 (9)−0.0004 (7)−0.0079 (8)−0.0027 (7)
C40.0200 (11)0.0197 (11)0.0154 (10)0.0025 (8)0.0005 (8)−0.0043 (8)
C10.0139 (10)0.0159 (10)0.0162 (10)−0.0007 (8)0.0038 (8)−0.0009 (8)
C150.0237 (12)0.0244 (12)0.0265 (12)0.0012 (9)0.0015 (9)0.0031 (10)
C20.0126 (9)0.0151 (10)0.0144 (10)0.0010 (8)0.0004 (8)0.0007 (8)
C60.0129 (9)0.0176 (10)0.0180 (10)−0.0015 (8)0.0020 (8)0.0019 (8)
C50.0162 (10)0.0147 (10)0.0220 (11)−0.0014 (8)−0.0022 (8)−0.0016 (8)

Geometric parameters (Å, °)

Co1—O1i2.0386 (16)N1—C11.315 (3)
Co1—O12.0386 (16)N1—C21.400 (3)
Co1—O22.4163 (18)C10—C91.385 (3)
Co1—O2i2.4163 (18)C10—H100.9300
Co1—N12.0709 (16)C13—C81.384 (3)
Co1—N1i2.0709 (16)C13—H130.9300
O1—C141.253 (3)C8—C91.384 (3)
C11—C121.393 (3)C9—H90.9300
C11—C101.398 (3)C14—O21.245 (3)
C11—C11ii1.486 (4)C14—C151.516 (3)
C12—C131.387 (3)C4—C51.403 (3)
C12—H120.9300C4—H40.9300
C7—C61.390 (3)C1—H10.9300
C7—N21.392 (2)C15—H15A0.9600
C7—C21.402 (3)C15—H15B0.9600
C3—C41.383 (3)C15—H15C0.9600
C3—C21.394 (3)C6—C51.377 (3)
C3—H30.9300C6—H60.9300
N2—C11.356 (3)C5—H50.9300
N2—C81.428 (2)
O1i—Co1—O1143.29 (10)C9—C8—C13120.90 (18)
O1i—Co1—N1106.93 (7)C9—C8—N2119.55 (17)
O1—Co1—N195.21 (6)C13—C8—N2119.55 (17)
O1i—Co1—N1i95.21 (6)C8—C9—C10119.21 (18)
O1—Co1—N1i106.93 (7)C8—C9—H9120.4
N1—Co1—N1i105.34 (9)C10—C9—H9120.4
C14—O1—Co198.41 (13)O2—C14—O1122.0 (2)
C12—C11—C10118.47 (18)O2—C14—C15120.16 (19)
C12—C11—C11ii121.45 (13)O1—C14—C15117.86 (18)
C10—C11—C11ii120.07 (13)C3—C4—C5121.67 (19)
C13—C12—C11120.84 (18)C3—C4—H4119.2
C13—C12—H12119.6C5—C4—H4119.2
C11—C12—H12119.6N1—C1—N2113.41 (18)
C6—C7—N2132.25 (18)N1—C1—H1123.3
C6—C7—C2122.45 (18)N2—C1—H1123.3
N2—C7—C2105.27 (17)C14—C15—H15A109.5
C4—C3—C2117.29 (18)C14—C15—H15B109.5
C4—C3—H3121.4H15A—C15—H15B109.5
C2—C3—H3121.4C14—C15—H15C109.5
C1—N2—C7106.87 (16)H15A—C15—H15C109.5
C1—N2—C8126.16 (17)H15B—C15—H15C109.5
C7—N2—C8126.95 (16)C3—C2—N1130.35 (18)
C1—N1—C2105.12 (16)C3—C2—C7120.32 (19)
C1—N1—Co1123.02 (14)N1—C2—C7109.32 (17)
C2—N1—Co1131.69 (13)C5—C6—C7116.59 (18)
C9—C10—C11121.05 (19)C5—C6—H6121.7
C9—C10—H10119.5C7—C6—H6121.7
C11—C10—H10119.5C6—C5—C4121.67 (19)
C8—C13—C12119.46 (18)C6—C5—H5119.2
C8—C13—H13120.3C4—C5—H5119.2
C12—C13—H13120.3
O1i—Co1—O1—C14−43.39 (12)C13—C8—C9—C10−2.3 (3)
N1—Co1—O1—C14−171.08 (13)N2—C8—C9—C10177.49 (18)
N1i—Co1—O1—C1481.14 (14)C11—C10—C9—C81.1 (3)
C10—C11—C12—C13−2.7 (3)Co1—O1—C14—O2−6.9 (2)
C11ii—C11—C12—C13176.7 (2)Co1—O1—C14—C15172.84 (15)
C6—C7—N2—C1178.2 (2)C2—C3—C4—C50.5 (3)
C2—C7—N2—C10.0 (2)C2—N1—C1—N2−1.1 (2)
C6—C7—N2—C8−3.3 (3)Co1—N1—C1—N2−176.94 (13)
C2—C7—N2—C8178.53 (18)C7—N2—C1—N10.7 (2)
O1i—Co1—N1—C1−49.07 (17)C8—N2—C1—N1−177.81 (17)
O1—Co1—N1—C1101.29 (16)C4—C3—C2—N1178.6 (2)
N1i—Co1—N1—C1−149.55 (18)C4—C3—C2—C7−0.5 (3)
O1i—Co1—N1—C2136.34 (17)C1—N1—C2—C3−178.1 (2)
O1—Co1—N1—C2−73.29 (18)Co1—N1—C2—C3−2.8 (3)
N1i—Co1—N1—C235.86 (15)C1—N1—C2—C71.1 (2)
C12—C11—C10—C91.4 (3)Co1—N1—C2—C7176.39 (13)
C11ii—C11—C10—C9−178.0 (2)C6—C7—C2—C30.2 (3)
C11—C12—C13—C81.5 (3)N2—C7—C2—C3178.57 (17)
C12—C13—C8—C91.0 (3)C6—C7—C2—N1−179.06 (18)
C12—C13—C8—N2−178.74 (17)N2—C7—C2—N1−0.7 (2)
C1—N2—C8—C9131.6 (2)N2—C7—C6—C5−177.7 (2)
C7—N2—C8—C9−46.6 (3)C2—C7—C6—C50.2 (3)
C1—N2—C8—C13−48.6 (3)C7—C6—C5—C4−0.3 (3)
C7—N2—C8—C13133.1 (2)C3—C4—C5—C6−0.1 (3)

Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1, y, −z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5708).

References

  • Jin, C. M., Lu, H., Wu, L. Y. & Huang, J. (2006). Chem. Commun. pp. 5039–5041. [PubMed]
  • Li, Z. X., Hu, T. L., Ma, H., Zeng, Y. F., Li, C. J., Tong, M. L. & Bu, X. H. (2010). Cryst. Growth Des.10, 1138–1144.
  • Rigaku/MSC (2005). CrystalClear Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Su, C. Y., Cai, Y. P., Chen, C. L., Smith, M. D., Kaim, W. & zur Loye, H. C. (2003). J. Am. Chem. Soc.125, 8595–8613. [PubMed]

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